(E)-3-Anilino-2-benzoyl-3-(methyl­sulfan­yl)acrylonitrile

Abdel-Aziz, H.A.; Ghabbour, H.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812013475

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1271

doi:10.1107/S1600536812013475

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(E)-3-Anilino-2-benzoyl-3-(methylsulfanyl)acrylonitrile

Hatem A. Abdel-Aziz,^a Hazem A. Ghabbour,^a Suchada Chantrapromma ^b ‡ and Hoong-Kun Fun ^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 27 March 2012; accepted 28 March 2012; online 31 March 2012)

In the title acrylonitrile derivative, C₁₇H₁₄N₂OS, the central aminoacrylaldehyde O=C—C=C—NH unit, wherein an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif, is approximately planar, with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms. This plane makes dihedral angles of 41.04 (9) and 84.86 (10)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 54.82 (10)°. An intramolecular C—H⋯N hydrogen bond is also present. In the crystal, weak C—H⋯π and π–π interactions, with a centroid–centroid distance of 3.8526 (14) Å, are observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002 ); Sączewski et al. (2004 ); Sommen et al. (2002 , 2003 ); Rudorf & Augustin (1977 ).

Experimental

Crystal data

C₁₇H₁₄N₂OS
M_r = 294.37
Monoclinic, P 2₁ /c
a = 8.7522 (2) Å
b = 10.8464 (3) Å
c = 16.1156 (4) Å
β = 103.968 (2)°
V = 1484.62 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.93 mm⁻¹
T = 296 K
0.58 × 0.52 × 0.34 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.401, T_max = 0.556
9777 measured reflections
2603 independent reflections
2403 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.04
2603 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.91 (3)	1.86 (3)	2.610 (2)	137 (2)
C11—H11B⋯N2	0.96	2.60	3.372 (2)	138
C17—H17A⋯Cg1ⁱ	0.93	2.91	3.690 (2)	143
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013475/is5105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013475/is5105Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013475/is5105Isup3.cml

checkCIF report

Comment top

Acrylonitrile derivatives play many important roles in chemistry such as in membrane technology (Saufi & Ismail, 2002), synthesis and medicinal chemistry (Sączewski et al., 2004; Sommen et al., 2002, 2003). 2,3-Disubstituted acrylonitriles represent an interesting class of biologically active compounds, many of them possess cytotoxicity (Sączewski et al., 2004). These interesting acrylonitrile derivatives promted us to synthesize the title acrylonitrile derivative (I) in order to study for its biological activity. Herein the crystal structure of (I) was reported.

The molecule of the title acrylonitrile derivative, C₁₇H₁₄N₂OS, exists in an E configuration with respect to the olifinic C8═C9 double bond [1.412 (2) Å] and with torsion angles C10–C8–C9–N1 = 162.52 (16)° and C7–C8–C9–S1 = 173.43 (12)° (Fig. 1). The molecule is twisted with the dihedral angle between the two phenyl rings being 54.82 (10)°. Atoms of the middle fragment of the central aminoacrylaldehyde unit (C7–C9/O1/N1) lie roughly on the same plane with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms (C7–C9/O1/N1). An intramolecular N1—H1N1···O1 hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995), which helps to stabilize the planarity of this plane. The mean plane through the C7/C8/C9/O1/N1 atoms makes dihedral angles of 41.04 (9) and 84.86 (10)° with the benzoyl and aminophenyl rings, respectively. The orientation of the methylthio group with respect to the olefinic moiety is indicated by the torsion angle C11–S1–C9–C8 = -42.56 (16)°. The dihedral angle between the two mean planes of N2/C10/C8/C9 and C8/C9/S1/C11 is 47.08 (15)°. An intramolecular weak C—H···N interaction generates an S(7) ring motif (Bernstein et al., 1995). The bond distances of (I) are within normal ranges (Allen et al., 1987).

The crystal packing of (I) is stabilized by weak C—H···π interactions (Table 1). A π–π interaction (Fig. 2) between the two aminophenyl rings with the distance of Cg2···Cg2ⁱⁱ = 3.8526 (14) Å [symmetry code (ii) = 1-x, 1-y, -z] was presented; Cg2 is the centroid of the C12–C17 ring.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002); Sączewski et al. (2004); Sommen et al. (2002, 2003); Rudorf & Augustin (1977).

Experimental top

The title compound was prepared according to the reported method (Rudorf et al., 1977). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.

Structure description top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002); Sączewski et al. (2004); Sommen et al. (2002, 2003); Rudorf & Augustin (1977).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular N—H···O hydrogen bond is shown as a dash line.
	Fig. 2. A crystal packing diagram of the title compound, viewed along the approximately along the a axis, showing the π–π interaction (dashed line) between the aminophenyl rings. H atoms were omitted for clarity.

(E)-3-Anilino-2-benzoyl-3-(methylsulfanyl)acrylonitrile top

Crystal data top

C₁₇H₁₄N₂OS	F(000) = 616
M_r = 294.37	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2603 reflections
a = 8.7522 (2) Å	θ = 5.0–67.5°
b = 10.8464 (3) Å	µ = 1.93 mm⁻¹
c = 16.1156 (4) Å	T = 296 K
β = 103.968 (2)°	Block, colorless
V = 1484.62 (7) Å³	0.58 × 0.52 × 0.34 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2603 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 67.5°, θ_min = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→10
T_min = 0.401, T_max = 0.556	k = −12→12
9777 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0633P)² + 0.3429P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2603 reflections	Δρ_max = 0.23 e Å⁻³
197 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (8)

Crystal data top

C₁₇H₁₄N₂OS	V = 1484.62 (7) Å³
M_r = 294.37	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.7522 (2) Å	µ = 1.93 mm⁻¹
b = 10.8464 (3) Å	T = 296 K
c = 16.1156 (4) Å	0.58 × 0.52 × 0.34 mm
β = 103.968 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2603 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2403 reflections with I > 2σ(I)
T_min = 0.401, T_max = 0.556	R_int = 0.024
9777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.23 e Å⁻³
2603 reflections	Δρ_min = −0.23 e Å⁻³
197 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.26713 (5)	0.35557 (4)	0.12096 (3)	0.05369 (19)
O1	0.76575 (17)	0.35293 (12)	0.07292 (10)	0.0674 (4)
N1	0.48494 (19)	0.25937 (13)	0.05485 (10)	0.0525 (4)
N2	0.4752 (2)	0.65992 (13)	0.16908 (13)	0.0639 (4)
C1	0.84541 (18)	0.53504 (14)	0.14953 (10)	0.0427 (4)
C2	0.9477 (2)	0.57125 (16)	0.10025 (11)	0.0520 (4)
H2A	0.9370	0.5375	0.0461	0.062*
C3	1.0652 (2)	0.65671 (18)	0.13054 (15)	0.0630 (5)
H3A	1.1317	0.6813	0.0965	0.076*
C4	1.0834 (2)	0.70502 (17)	0.21094 (15)	0.0649 (5)
H4A	1.1628	0.7621	0.2316	0.078*
C5	0.9841 (2)	0.66911 (18)	0.26115 (13)	0.0605 (5)
H5A	0.9977	0.7016	0.3159	0.073*
C6	0.8640 (2)	0.58504 (16)	0.23089 (11)	0.0507 (4)
H6A	0.7964	0.5623	0.2648	0.061*
C7	0.7250 (2)	0.43946 (15)	0.11312 (10)	0.0471 (4)
C8	0.56634 (19)	0.45013 (14)	0.12432 (10)	0.0439 (4)
C9	0.4545 (2)	0.35497 (13)	0.09959 (10)	0.0438 (4)
C10	0.51581 (19)	0.56593 (14)	0.15039 (11)	0.0469 (4)
C11	0.3008 (2)	0.40943 (17)	0.22941 (11)	0.0557 (4)
H11A	0.2120	0.3887	0.2519	0.084*
H11B	0.3146	0.4973	0.2307	0.084*
H11C	0.3937	0.3711	0.2635	0.084*
C12	0.3870 (2)	0.15146 (13)	0.03407 (11)	0.0446 (4)
C13	0.4078 (3)	0.05512 (18)	0.09040 (12)	0.0640 (5)
H13A	0.4838	0.0595	0.1418	0.077*
C14	0.3149 (3)	−0.04908 (18)	0.07019 (14)	0.0696 (6)
H14A	0.3281	−0.1148	0.1083	0.084*
C15	0.2036 (3)	−0.05567 (17)	−0.00557 (13)	0.0624 (5)
H15A	0.1411	−0.1256	−0.0189	0.075*
C16	0.1846 (3)	0.04131 (19)	−0.06189 (13)	0.0680 (5)
H16A	0.1087	0.0369	−0.1133	0.082*
C17	0.2775 (3)	0.14547 (16)	−0.04263 (12)	0.0580 (5)
H17A	0.2659	0.2106	−0.0812	0.070*
H1N1	0.578 (3)	0.265 (2)	0.0390 (16)	0.083 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0462 (3)	0.0578 (3)	0.0579 (3)	−0.00653 (16)	0.01425 (19)	−0.01599 (17)
O1	0.0598 (8)	0.0556 (8)	0.0942 (10)	−0.0063 (6)	0.0328 (7)	−0.0289 (7)
N1	0.0539 (9)	0.0434 (7)	0.0649 (9)	−0.0093 (6)	0.0235 (7)	−0.0163 (6)
N2	0.0534 (9)	0.0381 (8)	0.1009 (13)	−0.0011 (6)	0.0200 (8)	−0.0108 (7)
C1	0.0400 (8)	0.0378 (7)	0.0502 (8)	0.0055 (6)	0.0105 (6)	0.0008 (6)
C2	0.0481 (9)	0.0536 (9)	0.0564 (9)	0.0045 (7)	0.0164 (7)	−0.0001 (7)
C3	0.0478 (10)	0.0568 (11)	0.0874 (14)	−0.0016 (8)	0.0224 (9)	0.0082 (9)
C4	0.0455 (9)	0.0486 (10)	0.0956 (14)	−0.0029 (7)	0.0071 (9)	−0.0058 (9)
C5	0.0538 (10)	0.0562 (10)	0.0638 (11)	0.0083 (8)	−0.0007 (8)	−0.0141 (8)
C6	0.0484 (9)	0.0517 (9)	0.0516 (9)	0.0048 (7)	0.0111 (7)	−0.0011 (7)
C7	0.0495 (9)	0.0400 (8)	0.0528 (9)	0.0006 (7)	0.0140 (7)	−0.0032 (6)
C8	0.0449 (8)	0.0358 (7)	0.0513 (8)	−0.0014 (6)	0.0123 (7)	−0.0048 (6)
C9	0.0474 (9)	0.0384 (8)	0.0448 (8)	0.0001 (6)	0.0094 (6)	−0.0016 (6)
C10	0.0422 (8)	0.0379 (8)	0.0602 (9)	−0.0042 (6)	0.0115 (7)	−0.0026 (7)
C11	0.0698 (11)	0.0484 (9)	0.0520 (9)	−0.0024 (8)	0.0207 (8)	−0.0035 (7)
C12	0.0482 (9)	0.0361 (8)	0.0520 (9)	−0.0015 (6)	0.0170 (7)	−0.0088 (6)
C13	0.0721 (12)	0.0561 (10)	0.0566 (10)	−0.0033 (9)	0.0014 (9)	0.0047 (8)
C14	0.0857 (14)	0.0452 (10)	0.0781 (13)	−0.0034 (9)	0.0200 (11)	0.0149 (9)
C15	0.0684 (12)	0.0427 (9)	0.0803 (13)	−0.0132 (8)	0.0260 (10)	−0.0120 (8)
C16	0.0713 (12)	0.0612 (11)	0.0638 (11)	−0.0144 (9)	0.0015 (9)	−0.0082 (9)
C17	0.0689 (12)	0.0443 (9)	0.0576 (10)	−0.0052 (8)	0.0089 (9)	0.0030 (7)

Geometric parameters (Å, º) top

S1—C9	1.7549 (17)	C6—H6A	0.9300
S1—C11	1.7983 (17)	C7—C8	1.447 (2)
O1—C7	1.241 (2)	C8—C9	1.412 (2)
N1—C9	1.326 (2)	C8—C10	1.428 (2)
N1—C12	1.441 (2)	C11—H11A	0.9600
N1—H1N1	0.91 (3)	C11—H11B	0.9600
N2—C10	1.144 (2)	C11—H11C	0.9600
C1—C2	1.389 (2)	C12—C13	1.367 (3)
C1—C6	1.392 (2)	C12—C17	1.371 (3)
C1—C7	1.494 (2)	C13—C14	1.385 (3)
C2—C3	1.383 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.367 (3)
C3—C4	1.371 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.373 (3)
C4—C5	1.379 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.383 (3)
C5—C6	1.388 (3)	C16—H16A	0.9300
C5—H5A	0.9300	C17—H17A	0.9300

C9—S1—C11	104.50 (9)	N1—C9—C8	120.54 (16)
C9—N1—C12	125.09 (15)	N1—C9—S1	115.44 (13)
C9—N1—H1N1	114.4 (17)	C8—C9—S1	123.98 (12)
C12—N1—H1N1	120.4 (17)	N2—C10—C8	178.1 (2)
C2—C1—C6	118.92 (15)	S1—C11—H11A	109.5
C2—C1—C7	117.55 (14)	S1—C11—H11B	109.5
C6—C1—C7	123.47 (15)	H11A—C11—H11B	109.5
C3—C2—C1	120.98 (17)	S1—C11—H11C	109.5
C3—C2—H2A	119.5	H11A—C11—H11C	109.5
C1—C2—H2A	119.5	H11B—C11—H11C	109.5
C4—C3—C2	119.76 (19)	C13—C12—C17	120.98 (16)
C4—C3—H3A	120.1	C13—C12—N1	119.33 (16)
C2—C3—H3A	120.1	C17—C12—N1	119.67 (15)
C3—C4—C5	120.06 (17)	C12—C13—C14	119.40 (18)
C3—C4—H4A	120.0	C12—C13—H13A	120.3
C5—C4—H4A	120.0	C14—C13—H13A	120.3
C4—C5—C6	120.69 (18)	C15—C14—C13	120.27 (18)
C4—C5—H5A	119.7	C15—C14—H14A	119.9
C6—C5—H5A	119.7	C13—C14—H14A	119.9
C5—C6—C1	119.58 (17)	C14—C15—C16	119.79 (17)
C5—C6—H6A	120.2	C14—C15—H15A	120.1
C1—C6—H6A	120.2	C16—C15—H15A	120.1
O1—C7—C8	122.07 (15)	C15—C16—C17	120.44 (18)
O1—C7—C1	117.75 (15)	C15—C16—H16A	119.8
C8—C7—C1	120.17 (13)	C17—C16—H16A	119.8
C9—C8—C10	118.88 (15)	C12—C17—C16	119.11 (17)
C9—C8—C7	121.80 (14)	C12—C17—H17A	120.4
C10—C8—C7	118.79 (14)	C16—C17—H17A	120.4

C6—C1—C2—C3	−0.8 (2)	C12—N1—C9—S1	−9.1 (2)
C7—C1—C2—C3	−178.16 (16)	C10—C8—C9—N1	162.52 (16)
C1—C2—C3—C4	1.2 (3)	C7—C8—C9—N1	−9.0 (2)
C2—C3—C4—C5	−0.5 (3)	C10—C8—C9—S1	−15.0 (2)
C3—C4—C5—C6	−0.7 (3)	C7—C8—C9—S1	173.43 (12)
C4—C5—C6—C1	1.0 (3)	C11—S1—C9—N1	139.77 (13)
C2—C1—C6—C5	−0.3 (2)	C11—S1—C9—C8	−42.56 (16)
C7—C1—C6—C5	176.88 (15)	C9—N1—C12—C13	−87.4 (2)
C2—C1—C7—O1	39.4 (2)	C9—N1—C12—C17	94.4 (2)
C6—C1—C7—O1	−137.81 (18)	C17—C12—C13—C14	−1.2 (3)
C2—C1—C7—C8	−139.89 (16)	N1—C12—C13—C14	−179.41 (19)
C6—C1—C7—C8	42.9 (2)	C12—C13—C14—C15	0.2 (3)
O1—C7—C8—C9	8.1 (3)	C13—C14—C15—C16	0.2 (3)
C1—C7—C8—C9	−172.59 (14)	C14—C15—C16—C17	0.2 (3)
O1—C7—C8—C10	−163.40 (17)	C13—C12—C17—C16	1.6 (3)
C1—C7—C8—C10	15.9 (2)	N1—C12—C17—C16	179.83 (18)
C12—N1—C9—C8	173.11 (16)	C15—C16—C17—C12	−1.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.91 (3)	1.86 (3)	2.610 (2)	137 (2)
C11—H11B···N2	0.96	2.60	3.372 (2)	138
C17—H17A···Cg1ⁱ	0.93	2.91	3.690 (2)	143

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂OS
M_r	294.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.7522 (2), 10.8464 (3), 16.1156 (4)
β (°)	103.968 (2)
V (Å³)	1484.62 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.58 × 0.52 × 0.34

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.401, 0.556
No. of measured, independent and observed [I > 2σ(I)] reflections	9777, 2603, 2403
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.04
No. of reflections	2603
No. of parameters	197
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.91 (3)	1.86 (3)	2.610 (2)	137 (2)
C11—H11B···N2	0.96	2.60	3.372 (2)	138
C17—H17A···Cg1ⁱ	0.93	2.91	3.690 (2)	143

Symmetry code: (i) −x+1, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and SC thank the Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rudorf, W.-D. & Augustin, M. (1977). J. Prakt. Chem. 319, 545–560. CrossRef CAS Web of Science Google Scholar
Sączewski, F., Reszka, P., Gdaniec, M., Grünert, R. & Bednarski, P. J. (2004). J. Med. Chem. 47, 3438–3449. Web of Science PubMed Google Scholar
Saufi, S. M. & Ismail, A. F. (2002). Songklanakarin J. Sci. Technol. 24(Suppl.), 843–854. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sommen, G., Comel, A. & Kirsch, G. (2002). Tetrahedron Lett. 43, 257–260. Web of Science CrossRef CAS Google Scholar
Sommen, G., Comel, A. & Kirsch, G. (2003). Tetrahedron, 59, 1557–1564. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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